Design and synthesis of luminescent poly(arylene vinylene)s and poly(arylene enthynylene)s

Abstract

Luminescent conjugated polymers like poly(arylene vinylene)s (PAV) and poly(arylene ethynylene)s (PAE) have been widely studied due to their versatile applicability, for example as chemosensors or as active component of light emitting diodes. Therefore, a synthetic challenge is to design and develop optimised polymers of increased efficiency. In the first part of this work side and main chains of poly(arylene vinylene)s were varied systematically to obtain soluble conjugated polymers of intrinsic microporosity (C-PIM) and aggregation-induced emission (AIE) activity. The obtained polymers were compared for understanding the structural requirements for the desired combination of properties. To get a deeper insight, model compounds were synthesized and used for comparison. The resulting poly(arylene vinylene)s showed SBET surface areas of up to 417 m2g-1 and AIE effects leading to high fluorescence efficiency. One polymer was applied in explosive sensing experiments where it proved its high sensitivity towards picric acid with a very low detection limit of 1.5 ppm. Furthermore, a N-carbazolyl-substituted poly(arylene vinylene) was electrooxidatively cross-linked and the influence of the cross-linking on optical properties and SBET surface areas was investigated. In the second part of this work a soluble poly(anthrylene ethynylene) was synthesized by a novel procedure. The polymer was characterized and compared to a monomeric model compound. Fluorescence anisotropy measurements revealed that the defined transition dipole moment of anthracene is blurred by the incorporation of the anthryl units into the polymer chain.